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MedKoo Cat#: 202590 | Name: Semapimod HCl
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Semapimod, known as CNI-1493, is a cytokine inhibitor. Semapimod is an investigational new drug which has anti-inflammatory, anti-cytokine, immunomodulatory, antiviral and antimalarial properties. Structurally, semapimod is synthetic guanylhydrazone mitogen-activated protein kinase blocker, as a potential treatment for Crohn's disease and other inflammatory conditions.

Chemical Structure

Semapimod HCl
CAS#164301-51-3 (HCl)

Theoretical Analysis

MedKoo Cat#: 202590

Name: Semapimod HCl

CAS#: 164301-51-3 (HCl)

Chemical Formula: C34H52N18O2

Exact Mass: 744.4521

Molecular Weight: 744.90

Elemental Analysis: C, 54.82; H, 7.04; N, 33.85; O, 4.30

Price and Availability

Size Price Availability Quantity
5mg USD 190.00 Ready to ship
10mg USD 350.00 Ready to ship
25mg USD 550.00 Ready to ship
50mg USD 950.00 Ready to ship
100mg USD 1,750.00 Ready to ship
200mg USD 2,950.00 Ready to ship
500mg USD 3,850.00 Ready to ship
1g USD 4,950.00 Ready to ship
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Related CAS #
164301-51-3 (HCl) 352513-83-8 (free base) 872830-76-7 (HCl hydrate) 872830-80-3 (mesylate)
Synonym
CNI1493; CNI-1493; CNI1493; AXD-455; AXD 455; AXD455; AIDS121302; AIDS-121302; Semapimod HCl.
IUPAC/Chemical Name
N1,N10-bis(3-(1-(2-carbamimidoylhydrazono)ethyl)-5-(1-(2-carbamimidoylhydrazono)ethyl)phenyl)decanediamide, tetrahydrochloride
InChi Key
MAHASPGBAIQZLY-RTQZJKMDSA-N
InChi Code
InChI=1S/C34H52N18O2.4ClH/c1-19(45-49-31(35)36)23-13-24(20(2)46-50-32(37)38)16-27(15-23)43-29(53)11-9-7-5-6-8-10-12-30(54)44-28-17-25(21(3)47-51-33(39)40)14-26(18-28)22(4)48-52-34(41)42;;;;/h13-18H,5-12H2,1-4H3,(H,43,53)(H,44,54)(H4,35,36,49)(H4,37,38,50)(H4,39,40,51)(H4,41,42,52);4*1H/b45-19+,46-20+,47-21+,48-22+;;;;
SMILES Code
O=C(NC1=CC(/C(C)=N/NC(N)=N)=CC(/C(C)=N/NC(N)=N)=C1)CCCCCCCCC(NC2=CC(/C(C)=N/NC(N)=N)=CC(/C(C)=N/NC(N)=N)=C2)=O.[H]Cl.[H]Cl.[H]Cl.[H]Cl
Appearance
white solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in water
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Related CAS# CAS#164301-51-3 (Semapimod HCl). CAS#352513-83-8 (Semapimod free base).    
Biological target:
Semapimod tetrahydrochloride (CNI-1493), an inhibitor of proinflammatory cytokine production, can inhibit TNF-α, IL-1β, and IL-6 with an IC50≈0.3 μM for TLR4.
In vitro activity:
In primary enterocyte cell culture, Semapimod inhibits signaling by agonists of Toll-like receptors TLR2, 4 and 9, but not by TLR5 agonist, the inflammatory cytokine IL-1β, or cellular stresses. Effects of Semapimod on responses to LPS are dose-dependent with regard to concentrations of both Semapimod and LPS. In cells treated with Semapimod, higher concentrations of LPS are required to elicit the same response than in untreated cells, and Semapimod fails to block responses to LPS applied at concentrations of 5 μg/ml or higher. gp96, an ER-associated chaperone of the HSP90 family, which is critically involved in assembly and trafficking of the TLR signaling complexes, was identified as a target of Semapimod using a pull-down assay for the ATP-binding proteins. Semapimod inhibits ATP binding and ATPase activity of purified gp96 in a dose-dependent fashion in vitro. Reference: J Immunol. 2016 Jun 15; 196(12): 5130–5137. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4896225/
In vivo activity:
In the animal model, CNI-1493 treatment yielded a modest reduction in the size of primary tumors. It is likely that this small decrease only partially accounts for the robust reduction in invasive metastases seen in the lung parenchyma. Inhibitory effects of CNI-1493 on intravasation at the primary site cannot be ruled out, but if egress from the primary site were the principal mechanism of action of CNI-1493, drug treatment would have resulted in fewer metastases with similar extents of invasion. However, this study observed intravascular metastases with noninvasive morphologies in CNI-1493-treated mice, strongly suggesting that the primary effect of CNI-1493 consists of inhibiting extravasation. Reference: PLoS One. 2015; 10(12): e0145197. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4692435/
Solvent mg/mL mM comments
Solubility
Water 14.3 19.18
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 744.90 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Wang J, Grishin AV, Ford HR. Experimental Anti-Inflammatory Drug Semapimod Inhibits TLR Signaling by Targeting the TLR Chaperone gp96. J Immunol. 2016 Jun 15;196(12):5130-7. doi: 10.4049/jimmunol.1502135. Epub 2016 May 18. PMID: 27194788; PMCID: PMC4896225. 2. Sankowski R, Herring A, Keyvani K, Frenzel K, Wu J, Röskam S, Noelker C, Bacher M, Al-Abed Y. The multi-target effects of CNI-1493: convergence of anti-amylodogenic and anti-inflammatory properties in animal models of Alzheimer's disease. Mol Med. 2016 Dec;22:776-788. doi: 10.2119/molmed.2016.00163. Epub 2016 Nov 15. PMID: 27847962; PMCID: PMC5193463. 3. Hesketh AJ, Maloney C, Behr CA, Edelman MC, Glick RD, Al-Abed Y, Symons M, Soffer SZ, Steinberg BM. The Macrophage Inhibitor CNI-1493 Blocks Metastasis in a Mouse Model of Ewing Sarcoma through Inhibition of Extravasation. PLoS One. 2015 Dec 28;10(12):e0145197. doi: 10.1371/journal.pone.0145197. PMID: 26709919; PMCID: PMC4692435 4. Bach JP, Mengel D, Wahle T, Kautz A, Balzer-Geldsetzer M, Al-Abed Y, Dodel R, Bacher M. The role of CNI-1493 in the function of primary microglia with respect to amyloid-β. J Alzheimers Dis. 2011;26(1):69-80. doi: 10.3233/JAD-2011-110179. PMID: 21593565.
In vitro protocol:
1. Wang J, Grishin AV, Ford HR. Experimental Anti-Inflammatory Drug Semapimod Inhibits TLR Signaling by Targeting the TLR Chaperone gp96. J Immunol. 2016 Jun 15;196(12):5130-7. doi: 10.4049/jimmunol.1502135. Epub 2016 May 18. PMID: 27194788; PMCID: PMC4896225. 2. Bach JP, Mengel D, Wahle T, Kautz A, Balzer-Geldsetzer M, Al-Abed Y, Dodel R, Bacher M. The role of CNI-1493 in the function of primary microglia with respect to amyloid-β. J Alzheimers Dis. 2011;26(1):69-80. doi: 10.3233/JAD-2011-110179. PMID: 21593565.
In vivo protocol:
1. Sankowski R, Herring A, Keyvani K, Frenzel K, Wu J, Röskam S, Noelker C, Bacher M, Al-Abed Y. The multi-target effects of CNI-1493: convergence of anti-amylodogenic and anti-inflammatory properties in animal models of Alzheimer's disease. Mol Med. 2016 Dec;22:776-788. doi: 10.2119/molmed.2016.00163. Epub 2016 Nov 15. PMID: 27847962; PMCID: PMC5193463. 2. Hesketh AJ, Maloney C, Behr CA, Edelman MC, Glick RD, Al-Abed Y, Symons M, Soffer SZ, Steinberg BM. The Macrophage Inhibitor CNI-1493 Blocks Metastasis in a Mouse Model of Ewing Sarcoma through Inhibition of Extravasation. PLoS One. 2015 Dec 28;10(12):e0145197. doi: 10.1371/journal.pone.0145197. PMID: 26709919; PMCID: PMC4692435.
1: Zheng EJ, Valeri JA, Andrews IW, Krishnan A, Bandyopadhyay P, Anahtar MN, Herneisen A, Schulte F, Linnehan B, Wong F, Stokes JM, Renner LD, Lourido S, Collins JJ. Discovery of antibiotics that selectively kill metabolically dormant bacteria. Cell Chem Biol. 2024 Apr 18;31(4):712-728.e9. doi: 10.1016/j.chembiol.2023.10.026. Epub 2023 Nov 28. PMID: 38029756; PMCID: PMC11031330. 2: Sankowski R, Herring A, Keyvani K, Frenzel K, Wu J, Röskam S, Noelker C, Bacher M, Al-Abed Y. The multi-target effects of CNI-1493: convergence of anti- amylodogenic and anti-inflammatory properties in animal models of Alzheimer's disease. Mol Med. 2016 Dec;22:776-788. doi: 10.2119/molmed.2016.00163. Epub 2016 Nov 15. PMID: 27847962; PMCID: PMC5193463. 3: Coniglio S, Miller I, Symons M, Segall JE. Coculture Assays to Study Macrophage and Microglia Stimulation of Glioblastoma Invasion. J Vis Exp. 2016 Oct 20;(116):53990. doi: 10.3791/53990. PMID: 27805587; PMCID: PMC5092226. 4: Wang J, Grishin AV, Ford HR. Experimental Anti-Inflammatory Drug Semapimod Inhibits TLR Signaling by Targeting the TLR Chaperone gp96. J Immunol. 2016 Jun 15;196(12):5130-7. doi: 10.4049/jimmunol.1502135. Epub 2016 May 18. PMID: 27194788; PMCID: PMC4896225. 5: Schröder M, Kolodzik A, Windshügel B, Krepstakies M, Priyadarshini P, Hartjen P, van Lunzen J, Rarey M, Hauber J, Meier C. Linker-Region Modified Derivatives of the Deoxyhypusine Synthase Inhibitor CNI-1493 Suppress HIV-1 Replication. Arch Pharm (Weinheim). 2016 Feb;349(2):91-103. doi: 10.1002/ardp.201500323. Epub 2016 Jan 3. PMID: 26725082. 6: Hesketh AJ, Maloney C, Behr CA, Edelman MC, Glick RD, Al-Abed Y, Symons M, Soffer SZ, Steinberg BM. The Macrophage Inhibitor CNI-1493 Blocks Metastasis in a Mouse Model of Ewing Sarcoma through Inhibition of Extravasation. PLoS One. 2015 Dec 28;10(12):e0145197. doi: 10.1371/journal.pone.0145197. PMID: 26709919; PMCID: PMC4692435. 7: Miller IS, Didier S, Murray DW, Turner TH, Issaivanan M, Ruggieri R, Al-Abed Y, Symons M. Semapimod sensitizes glioblastoma tumors to ionizing radiation by targeting microglia. PLoS One. 2014 May 9;9(5):e95885. doi: 10.1371/journal.pone.0095885. PMID: 24816734; PMCID: PMC4015930. 8: Vilz TO, Sommer N, Kahl P, Pantelis D, Kalff JC, Wehner S. Oral CPSI-2364 treatment prevents postoperative ileus in swine without impairment of anastomotic healing. Cell Physiol Biochem. 2013;32(5):1362-73. doi: 10.1159/000356575. Epub 2013 Nov 22. PMID: 24280834. 9: Websky Mv, Fujishiro J, Ohsawa I, Praktiknjo M, Wehner S, Abu-Elmagd K, Kitamura K, Kalff JC, Schaefer N, Pech T. The novel guanylhydrazone CPSI-2364 ameliorates ischemia reperfusion injury after experimental small bowel transplantation. Transplantation. 2013 Jun 15;95(11):1315-23. doi: 10.1097/TP.0b013e31828e72fa. PMID: 23598944. 10: Noelker C, Stuckenholz V, Reese JP, Alvarez-Fischer D, Sankowski R, Rausch T, Oertel WH, Hartmann A, van Patten S, Al-Abed Y, Bacher M. CNI-1493 attenuates neuroinflammation and dopaminergic neurodegeneration in the acute MPTP mouse model of Parkinson's disease. Neurodegener Dis. 2013;12(2):103-10. doi: 10.1159/000342714. Epub 2012 Nov 7. PMID: 23147695. 11: Erin N, Duymuş O, Oztürk S, Demir N. Activation of vagus nerve by semapimod alters substance P levels and decreases breast cancer metastasis. Regul Pept. 2012 Nov 10;179(1-3):101-8. doi: 10.1016/j.regpep.2012.08.001. Epub 2012 Sep 11. PMID: 22982142. 12: Wehner S, Vilz TO, Sommer N, Sielecki T, Hong GS, Lysson M, Stoffels B, Pantelis D, Kalff JC. The novel orally active guanylhydrazone CPSI-2364 prevents postoperative ileus in mice independently of anti-inflammatory vagus nerve signaling. Langenbecks Arch Surg. 2012 Oct;397(7):1139-47. doi: 10.1007/s00423-012-0989-6. Epub 2012 Aug 19. PMID: 22903876. 13: Ziegler P, Chahoud T, Wilhelm T, Pällman N, Braig M, Wiehle V, Ziegler S, Schröder M, Meier C, Kolodzik A, Rarey M, Panse J, Hauber J, Balabanov S, Brümmendorf TH. Evaluation of deoxyhypusine synthase inhibitors targeting BCR- ABL positive leukemias. Invest New Drugs. 2012 Dec;30(6):2274-83. doi: 10.1007/s10637-012-9810-1. Epub 2012 Mar 14. PMID: 22415796. 14: Oettinger CW, D'Souza MJ. Microencapsulated drug delivery: a new approach to pro-inflammatory cytokine inhibition. J Microencapsul. 2012;29(5):455-62. doi: 10.3109/02652048.2012.658443. Epub 2012 Feb 21. PMID: 22348221; PMCID: PMC3433085. 15: Bach JP, Mengel D, Wahle T, Kautz A, Balzer-Geldsetzer M, Al-Abed Y, Dodel R, Bacher M. The role of CNI-1493 in the function of primary microglia with respect to amyloid-β. J Alzheimers Dis. 2011;26(1):69-80. doi: 10.3233/JAD-2011-110179. PMID: 21593565. 16: Woriedh M, Hauber I, Martinez-Rocha AL, Voigt C, Maier FJ, Schröder M, Meier C, Hauber J, Schäfer W. Preventing Fusarium head blight of wheat and cob rot of maize by inhibition of fungal deoxyhypusine synthase. Mol Plant Microbe Interact. 2011 May;24(5):619-27. doi: 10.1094/MPMI-03-10-0068. PMID: 21463208. 17: The F, Cailotto C, van der Vliet J, de Jonge WJ, Bennink RJ, Buijs RM, Boeckxstaens GE. Central activation of the cholinergic anti-inflammatory pathway reduces surgical inflammation in experimental post-operative ileus. Br J Pharmacol. 2011 Jul;163(5):1007-16. doi: 10.1111/j.1476-5381.2011.01296.x. PMID: 21371006; PMCID: PMC3130947. 18: Vlachakis IK, Pitoulias GA, Kontopoulou KE, Kotakidou RE, Kosmidou EK, Kallaitzopoulou ME, Papadimitriou DK. Semapimod a new pretreatment modality of acute intestinal ischemia-reperfusion syndrome: experimental study in rabbits. Int Angiol. 2011 Feb;30(1):35-42. PMID: 21248671. 19: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2010 Nov;32(9):675-703. doi: 10.1358/mf.2010.32.9.1563109. PMID: 21225019. 20: dos Santos CC, Shan Y, Akram A, Slutsky AS, Haitsma JJ. Neuroimmune regulation of ventilator-induced lung injury. Am J Respir Crit Care Med. 2011 Feb 15;183(4):471-82. doi: 10.1164/rccm.201002-0314OC. Epub 2010 Sep 24. PMID: 20870758.